Pretty Handsome Awkward
by remyohh
Summary: All Simon wants to do is pass his advanced level classes, balance being a international rockstar with his home life, and just get with a girl already. In the wake of Alvin and Brittany's heated breakup, Brittany finds solace on his couch more than her own. And who is Simon to complain? Simon/Brittany AU. Hilarity and suggestive instances ensue.


A/N: So, here I am with a Chipmunks story. This has been floating around for a while and I finally just decided to post it. Brittany/Simon at their finest. Let me know what you think!

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He sighed again, looking over his textbook one more time before jotting down the annotations for his paper. All this work was kind of killing him, yes he knew what he was getting himself into when he signed up for the advanced college level classes, but, this was just getting ridiculous. He was uncommonly smart – that everyone knew – but, just because he was intelligent didn't mean he actually enjoyed doing all the work that came with it. At least, not anymore.

It was tough, juggling school work, being an international rockstar, rehearsals with Dave and Ms. Miller, attempting to actually make time for a social life...

He looked over to his nightstand, not finding the picture that used to reside there. It had been a picture of him and Jeanette, he wasn't actually sure who had taken it, but it had been one of the only times they were ever touchy-feely with one another, and it had just happened to make it on film.

That was basically the reason Jeanette and him broke up, they were both just so busy and he couldn't commit to her the way they both would've liked. It was a mutual agreement, he rolled his eyes at the thought, so cordial they were. That was another reason why they didn't work, while Jeanette was painfully shy, he was just quiet, he had a dry sarcasm that she didn't understand. Their whole relationship was like a business deal, scheduling time to be together, studying when they actually had those precious moments alone, there were no sly glances or soft whispers, hushed endearments or small smiles. Just cold, hard, silence, and intensely awkward encounters. And that was not how he wanted his relationship to be, and he knew that neither did she, or maybe she did, because apparently he didn't know Jeanette as well as he had previously thought. And, she hadn't known him all that well either – that was for sure.

He may have been a quiet, studious person, but he still wanted the intimacy of a girlfriend, and not even in just the sexual sense, although that he wouldn't mind that particular part either. He was seventeen years old, successful in the music industry, and painfully smart, yet he had barely even made out with a girl.

Yeah, that's what he said, nobody heard that wrong. He was a seventeen year old virgin, to basically everything but his own hand, destined to live the rest of his young years alone, sex deprived, emotionally unfulfilled, with his nose stuck in a book.

Could he choose death now, or...?

He let a growl escape his throat as he threw down his notebook and stalked out of his room, bounding down the stairs toward the kitchen. That's when he heard it, the small whisper of angry laments, the television quietly playing in the background, and the ever obvious sigh of discontent. He stuck his head into the living room and found the girl sitting on their couch, arms crossed over her full chest and feet propped up on the coffee table in font of her. Her full lips were set into an angry pout, her wide eyes set on the t.v. in front of her, even though he could tell she wasn't actually watching it.

This wasn't the first time he'd found Brittany Miller sitting on his couch, angrily staring at their tv set, he knew it wouldn't be the last, and for some reason he unconsciously took comfort in that. He also couldn't help glancing her over, it wasn't like he'd never looked at Brittany before, because he most certainly had, but he tried not to do it when she could potentially notice – cause seriously, she totally needed that extra air in her pretty little head of like he needed yet another notebook filled with quadratic equations. Or a hole in the head, which ever came first at this point.

And, again with the sarcasm.

It really was no secret that Brittany was attractive, she always had been, all the Miller girls were or had developed into anyway. But, Brittany had just always been more so, so much more classically beautiful. She wasn't as tall as Jeanette, not as lanky; her chest and hips not as thick or rounded as Eleanor's. Her legs were so long though, toned and slim, her waist thin with a flat stomach, paired with slightly rounded hips. He had noticed each perfectly sized, full, perky breast a time or two, as well as the hour-glass shape of her figure. Her eyes were wide and strikingly blue, her long hair was auburn in color and waved down to her chest, but she always had her hair up in that damned messy ponytail. Which had always seemed strange to him, someone who spent so much time on their appearance wearing any style messy, but that was just another oxymoronic thing about Brittany that he had yet to figure out.

He had noted when she had moved out of her all pink phase – just as he noted everything about everyone, as always – and when she had moved into a more _teen_ phase of her wardrobe. Although, when they performed she was still forced to wear all sparkles, glitter, and of course, pink. Because, they all still had to wear their standard colors in front of an audience, because they were still ten, apparently.

It was strange seeing Brittany so much though, of course he saw her a lot of the time anyway, but ever since her and Alvin broke up, well, she seemed to spend more time on his couch than her own. He knew why though, and he wasn't going to pretend any differently, not even for pity's sake, because she didn't deserve pity. She deserved so much more than that.

He eased himself into the room, coming to stop next to the couch, "Hey Brittany..."

She looked up at him, anger still evident in her bright eyes, but a gentle calm took over her face. "Simon," Her voice was calm and smooth, "What time is it?" He looked at the cable box that read ten past six, but knew that question was a rhetorical one. "Where is he?"

He sighed and sat down next to her on the arm of the couch, she was talking about Alvin and his recent habit of being late to all things Brittany related. It was no secret that Alvin and Brittany's breakup had been very public and very heated, making bad press for the lot of them when it had occurred. The pair had said some incredibly vicious things, Alvin more so than Brittany in that fight, but she had gotten a punch in to his face, thus ending that particular battle but starting the many more to come. All of this occurring in the school parking lot, the fight caught on a cell phone and was uploaded onto Youtube that night, and on E!News the next morning.

The joke though was really on Alvin and Brittany in the end, because all of them were locked into a contract, so although the Chipette was no longer paired with the Chipmunk romantically, they still had to be paired musically. Therefore, Alvin and Brittany still had to sing together, which meant they still had to practice together, which Alvin was constantly avoiding, which was why Brittany was angrily sitting on his couch more often as of late. One of those times being the very present, as she was very presently sitting on his couch, in a right state.

"I don't know Brittany. Probably where he always is – "

"At the Diner in town, I know. I know where he is and with who, I just don't understand why he's not here."

Simon leaned back into the sofa, getting more comfortable, this was probably going to be a while. "You know why Brittany, don't insult your own intelligence by pretending you don't know what Alvin is up too." Brittany sighed and did the same, leaning back into the couch, her shoulder unconsciously bumping against his. They weren't looking at each other, they weren't looking at the tv or even the slightly faded wall paper behind it, but they had the other's undivided attention. "Look Brittany, I'm not going to pretend that we're always the best of friends, and I'm not going to justify Alvin's actions, because quite frankly his actions are horrendous and he's acting like a toddler. But yes, ever since you broke up he's been more of a dick than he usually is, but, then again you did break his cheekbone."

"That's because he called me a lying slut in front of the whole school and now apparently the whole world! He lied about my reputation, making me out to be one of those 'hit it and quit it', _easy_ celebrities. He said things about me that weren't true Simon, a lot of mean things that weren't true, in front of everyone! I mean you said it yourself, we're not the best of friends all the time, but how long have you known me Simon? Do you really think I'd sleep with _anyone_ while going out with Alvin, especially the amount of guys he's saying I did, and apparently what I slept with them for?"

"Well, I don't think you'd sleep with the whole cast of Dancing with the Stars and Justin Bieber in one night anyway, but hey, that's just my opinion."

He saw her smile a bit out of the corner of his eye, he hadn't known how much of Alvin's bullshit really hurt her. He had always just figured that she'd curse at him and move on, she was tough, she was Brittany, she didn't take shit like that. And yet, here she was, sitting on his couch beside him, anger seeping off her in waves, waiting on Alvin. This wasn't like her, and she couldn't cover the sadness in her big, sea breeze colored eyes.

"We have to sing that duet you know, a _love_ song." The way she said love, like it was dirty, left a bad taste in her mouth. "I _so_ don't want to do it, I can't do it, not with him, not anymore."

Simon sighed, "I'm sure Alvin will come around before its time to perform, he may be a chode but he's not about to risk his career on a bad break up with you." Brittany nodded, knowing it was true. "You know..."

Brittany turned her head to look at him, his eyes impossibly blue, matching the color of his hoodie. How many times had she accidentally looked into those eyes and wondered how they could be real, how they had to be contacts, people said the same about her eyes, but it was Simon's that were the real amazing thing. He was sweet, and she realized growing up with him that she hadn't always been the kindest when it came to the bi-speckled boy, and it made her sad that no one had the close relationship with him like they all had with Theo, because Simone truly deserved it.

Her relationship with the boy sitting next to her was close to nonexistent, they talked - mostly when she was angry or upset, with him playing the therapist to her homicidal patient. But, he had been there for her over the years, through all the bullshit drama with Alvin – he was there. And she had been there for him when he broke up with Jeanette, he had seemed more upset about the fact that her sister hadn't cried than the fact that his relationship had actually ended.

She wondered though, that if the only reason he had actually talked to her about the situation with her sister was because she had been the first to find him. But, she tossed that thought out of her head as quickly as it had come, he didn't talk about his _feelings_ or anything really emotionally invested with anyone, not even his brothers. She guessed that because she had broke-down in front of him more than once, he felt more at ease to even remotely wince in her direction, where as he would never even think of doing that around anyone else.

Did it make her feel special? Hell fucking yeah. Did she enjoy the way it made her feel? Fuck yes. Did she understand it at all? That would be a big ole no.

Simon was just so _quiet_, in that painfully interesting sort of way that left her yearning to have him give her more

"Yes?"

He opened his mouth to say something, his eyes still boring into her's, but it was the slam of the front door that shook him from whatever stupor he had apparently been subjected to. He sat upright, bringing himself away from her and she realized that she missed the warmth his body had given off.

Alvin was a grade A dick-fucker, who she would _so_ never ever getting back together with – she mentally thanked Taylor Swift for that line. But, she missed having a boyfriend. She missed the comfort and the closeness, she missed the talks and the quite cuddles. Maybe that was why she was reacting so strangely to Simon, clearly that _had_ to be it.

She turned her head at the sound of voices filling the hall, Theodore and Ellie appeared, all smiles and light touches. She was so happy for her beautiful sister, she really was, Theo was a great guy who would love her unconditionally till the end of time. But, she couldn't help the small tinge of jealousy at the sight of them, she was jealous that they had managed to find each other so young in life. There was no doubt in her mind – or anyone's mind – that Ellie and Theo would remain together, she knew that when they got older, they'd marry. And, they'd be happy forever.

It was as romantic as it was nauseating.

They broke apart once they noticed that Simon and Brittany sat in the living room, surprise showing on their faces. "Oh, hey guys." Eleanor turned to face Theo, her brows furrowing in confusion, before turning back to the pair. "What're you doing here, Britt?"

Brittany knew that Eleanor was only wondering because she had planned to run upstairs of the empty house and makeout with Theodore. _Ew._ And now their plans had been foiled by the fuming Brittany and the helpful Simon.

Brittany sighed, "Alvin didn't show up for rehearsal,_ again_. Not that I'm surprised." She said that as a side-note to Simon. "So, I stopped by here to see if he was around, but of course, he wasn't."

Ellie's eyes were sympathetic as she stepped further into the living room, Brittany knew that her sister was aware of just how painful and annoying this whole scenario had been. "I'm sorry, Britt."

Theo came up beside her sister, his hands shoved into his pockets, a sorrowful expression set on his cute face. He always was the most empathetic out of them all, and it was always genuine. She admired that about Theodore, she was rarely honest when it came to her emotions – unless it was anger. That was the difference between her and Theo, people mistook her bluntness for honesty, while he was just true-blue.

"I'm sorry about him, Brittany. I don't know why he's being such an asshole about the situation. I'll talk to him if you want?"

"Thanks, Theo, but I don't think that's gonna help much. Alvin is dead set on being a douche bag and nothing is going to stop him until he's perfectly ready.

Simon regarded the maturity in her statement, whether she really felt that way or it was all for show, he was proud of her. "Nothing that messing up on stage won't fix."

Brittany smiled and nudged Simon's shoulder with her own. There it was, there was that smile.

Theo nodded at Simon's statement, "Well, I'll have a talk with him anyway. I don't want his stubbornness to mess up our stage show. People pay good money to come and see us, and I don't think its fair to give them anything less than our best."

Oh, Theo. She loved him.

"You tell him, Theo."

"Tell me what?"

They all turned to see Alvin standing in the doorway of the living room, hands in his pockets, looking all cool and collected. Fucking prick.

"Oh, nice of you to finally show up." Her tone was sharp, her eyes cold.

"Did I miss something?" Alvin smirked.

He was fucking _smirking_. Playing coy, trying to piss her off. Well, two could play at that game.

"Nope. I was just leaving." She stood from her spot on the couch, she looked down to Simon, who was looking between her and Alvin. "Simon, what're doing right now?"

He looked up at her, quirking a brow. She had a mean smile glinting in her eyes, oh, this could not be good. "I was studying – "

She cut him off. "So nothing? Good." She turned and looked away from Alvin, gazing down into his eyes. "Want to come rehearse with me?"

He tore his gaze away from her's to look past Eleanor and Theo – who were gazing at each other uncomfortably – to Alvin, who had his jaw locked and his eyes set on Brittany.

"Uh," He looked back up at Brittany, her bright eyes pleading with him. "Sure."

She smiled again, it was played up because Alvin was watching. He didn't like being a pawn in their twisted little game, he hoped that's not all he'd end up being.

"Great. Let's go." She pulled him up from the couch, walking past Theo and Ellie. "Bye guys, Elle – text me when you're coming home."

Eleanor just nodded, seemingly in shock about the whole situation. Theodore just looked vastly uncomfortable, he was the peace keeper, he didn't like when things were amiss in their group.

Simon grabbed his keys from the end table beside the stairs, he could feel all the eyes in the room on him. He didn't like it. "I'll see you later, Theo."

His brother gave a nod, "Yeah, I'll see you soon."

Ellie then proceeded to grab Theodore's arm and drag him up the stairs to his room, the location they had been headed to before being side tracked by the strange sight of Brittany and Simon sitting alone together. Brittany mentally thanked her sister for seemingly reading the situation and getting Theo out of there, and letting Brittany and Simon escape easily.

Brittany walked past Alvin, stopping beside him, her eyes narrowed, a small smile on her lips. "Leave me waiting again, and see what happens."

She pushed past him and strutted out the door, Simon followed after her, Alvin stopping him once he got to the door. "Dude!"

Simon just shrugged and shook his head, unsure of what he was doing. How could Alvin want to know what was going on, when Simon didn't even know?

He walked past his brother and out the door, Brittany was already seated in the passenger seat of his car, a coy smile playing at her lips. He knew it was because Alvin was watching, even if his brother was pretending he wasn't.

He ran around to the side of his car, slipping into the driver's seat and starting it up. He pulled onto the road and began to drive, where? Well, he wasn't quite sure of that either. What was he doing? Why was he doing this? He didn't like to be in the middle, he didn't even like to be involved. And here he was, sitting in a car with Brittany Miller, pissing off his brother, and helping cause the strangeness that had wafted over the group.

He looked over at Brittany, the confident smile had slipped from her lips, her eyes were set on nothing in particular, her brows furrowed in thought.

He supposed that's why he decided to just go with it, the look in those bright eyes. He didn't like to see Brittany weak, it was uncommon and made him feel uncomfortable. She was sharp, and quick, manipulating, and sometimes vicious. She had been rude to him on so many occasions, and he had been rude right back. He wanted the meanness back in her eyes, wanted to the fight return in them. He didn't like the sad, melancholy look that had overtaken them. That's why he hadn't put up a fight, he just couldn't stand to see someone as strong as Brittany defeated, especially by someone like, Alvin.

He just kept driving, hopefully she'd tell him where to go. If there was one thing Simon was sure of, it was that Brittany couldn't manage to stay quite for long.

He sighed, what had he gotten himself into?

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A/N: Oh, Simon, what do you think you're doing? Where do you think they'll end up next chapter? How do you think Alvin will react when Simon gets home? Or Jeanette for that matter? Let me know what you think! Reviews are golden.


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